20,059

Dukes County, MA Homes

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  • /9

    $2,450,000

    • Land
    • 5.37 Acres
    • $456,238 per Acre

    9 Maqua Way, Edgartown, MA 02539

    Chappaquiddick: Beautiful 5-acre parcel offering private frontage on Katama Bay. The generous-sized lot affords plenty of development flexibility, with the ability to capture the view from nearly any location. Located on Maqua Way, a quiet subdivision just off the paved road, the property is conveniently situated near all the Chappy favorites: beaches, trails, a community center, and Slip Away

    Katherine Donahue Sandpiper Realty Inc

    9 Maqua Way, Edgartown, MA 02539
  • /40

    $32,500 total monthly price

    • 6 Beds
    • 4.5 Baths
    • 3,222 Sq Ft
    • House for Rent

    100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

    Karen Overtoom Karen M. Overtoom R.E.

    100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568
  • /32

    $1,100,000 Sold Jun 27, 2025

    10 Kims Way, Oak Bluffs, MA 02568

    • 4 Beds
    • 2.5 Baths
    • 1,976 Sq Ft
    • Built 1985

    Last Sold Summary

    • 12% Below List Price
    • $557/SF
    • 156 Days On Market

    Last Listing Agent Michael Schweikert Ocean Park Realty, Inc.

    10 Kims Way, Oak Bluffs, MA 02568
    • /32

      Est $4,521,088 Not Listed For Sale

      225 Bigelow Rd, Vineyard Haven, MA 02568

      • 5 Beds
      • 8 Baths
      • 5,305 Sq Ft
      • Built 1976
      225 Bigelow Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 10% Above List Price
      • $773/SF
      • 56 Days On Market

      Last Sold Price $4,100,000

      Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's International Realty

  • /15

    $2,490,000

    • Land
    • 7.2 Acres
    • $345,833 per Acre

    3 Jacobs Neck Road (North Lot 1) Unit 2, Edgartown, MA 02539

    Build your dream home on the special 7.2 acre North lot 1 private wooded property with 1/2 ownership in the beautiful 4.5 acre meadow in the grand Boldwater Association(BWA) on the glorious Edgartown Great Pond with approx. 3,000 ft of private barrier beach. BWA is 40 homesites on 450 acres with 150 acres of conservation abutting another 1,500 acres of conservation and a few large estates - all

    Robert Kenney Tea Lane Associates

    3 Jacobs Neck Road (North Lot 1) Unit 2, Edgartown, MA 02539
  • /33

    $22,000 total monthly price

    • 3 Beds
    • 2.5 Baths
    • 2,800 Sq Ft
    • House for Rent

    2 Strikers Way Ch211, Chilmark, MA 02535

    SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable drip coffee maker with glass carafe. There is a coffee grinder provided in the

    Karen Overtoom Karen M. Overtoom R.E.

    2 Strikers Way Ch211, Chilmark, MA 02535
  • /22

    $435,000 Sold Aug 26, 2025

    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535

    • Land
    • 0.1 Acre
    • $4,350,000 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 18 Days On Market

    Last Listing Agent Emma Kiley Bryant Landmarks at TODAY Real Estate

    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    • /7

      Est $5,031,808 Not Listed For Sale

      3 Duarte Cir, Edgartown, MA 02539

      • 6 Beds
      • 7 Baths
      • 6,783 Sq Ft
      • Built 2023
      3 Duarte Cir, Edgartown, MA 02539

      Last Sold Summary

      • 12% Below List Price
      • $840/SF
      • 329 Days On Market

      Last Sold Price $5,700,000

      Last Listing Agent Michele Casavant Vineyard Village Realty

  • /43

    $14,500,000

    • 4 Beds
    • 4.5 Baths
    • 3,705 Sq Ft

    64 Squibnocket Farm Rd, Chilmark, MA 02535

    Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within

    Thomas Wallace Wallace & Co. Sotheby's

    64 Squibnocket Farm Rd, Chilmark, MA 02535
  • /20

    $16,800 total monthly price

    • 3 Beds
    • 2 Baths
    • 1,638 Sq Ft
    • House for Rent

    31 S Ridge Rd Ch218, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and

    Karen Overtoom Karen M. Overtoom R.E.

    31 S Ridge Rd Ch218, Chilmark, MA 02535
  • /2

    $5,375,000 Sold Nov 14, 2025

    37 Morse St, Edgartown, MA 02539

    • 4 Beds
    • 5.5 Baths
    • 2,911 Sq Ft
    • Built 1820

    Last Sold Summary

    • $1,846/SF
    • 0 Days On Market

    Current Estimated Value $5,275,516

    Last Listing Agent LINK Email Cache LINK

    37 Morse St, Edgartown, MA 02539
    • /20

      Est $1,667,999 Not Listed For Sale

      21 Bold Meadow Ln, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,971 Sq Ft
      • Built 1991
      21 Bold Meadow Ln, Edgartown, MA 02539

      Last Sold Summary

      • 21% Above List Price
      • $698/SF
      • 34 Days On Market

      Last Sold Price $1,375,000

      Last Listing Agent Martha Smith C McManus Realty Group

  • /27

    $8,500,000

    • 4 Beds
    • 6 Baths
    • 3,497 Sq Ft

    24 Katama Bay View Rd, Edgartown, MA 02539

    This classic New England waterview home is a true masterpiece of modern living. Nestled on a spacious and meticulously landscaped lot in Katama, this property offers the perfect blend of elegance, comfort, and convenience. The main house features three spacious and beautifully appointed bedrooms, each designed for relaxation and comfort. From the primary suite to the guest bedrooms, every room

    Tom Wallace Wallace & Co. Sotheby's International Realty

    24 Katama Bay View Rd, Edgartown, MA 02539
  • /31

    $40,000 total monthly price

    • 6 Beds
    • 6 Baths
    • 3,960 Sq Ft
    • House for Rent

    384 Middle Rd Ch222, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $10,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four

    Karen Overtoom Karen M. Overtoom R.E.

    384 Middle Rd Ch222, Chilmark, MA 02535
  • /19

    $1,095,000 Sold May 02, 2025

    31 Davis St, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,945 Sq Ft
    • Built 1966

    Last Sold Summary

    • 2% Above List Price
    • $563/SF
    • 5 Days On Market

    Current Estimated Value $1,148,561

    Last Listing Agent Sheila Morse Island Real Estate

    31 Davis St, Vineyard Haven, MA 02568
    • /32

      Est $2,755,429 Not Listed For Sale

      10 Codman Spring Rd, Edgartown, MA 02539

      • 4 Beds
      • 3.5 Baths
      • 2,101 Sq Ft
      • Built 1980
      10 Codman Spring Rd, Edgartown, MA 02539

      Last Sold Summary

      • 24% Above List Price
      • $1,059/SF
      • 9 Days On Market

      Last Sold Price $2,225,000

      Last Listing Agent Josseph Barkett Compass

  • /7

    $4,500,000

    • 15 Beds
    • 12.5 Baths
    • 7,250 Sq Ft

    11 Macs Ln, Tisbury, MA 02568

    A unique opportunity to own a one of a kind property complete with fourteen bedrooms, flanked with large picture windows and water views from all three living levels. Currently being run as a state licensed, private pay, assisted living facility. In addition to the fourteen bedrooms and twelve full baths and one half bath, in the main building, there is a private owners apartment on the first

    Madelyn Silvia Wallace & Co. Sotheby's International Realty

    11 Macs Ln, Tisbury, MA 02568
  • /32

    $42,000 total monthly price

    • 5 Beds
    • 2.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    19 Lake Rd, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers 5 five bedrooms all with views, two livingrooms,

    Karen Overtoom Karen M. Overtoom R.E.

    19 Lake Rd, Chilmark, MA 02535
  • /2

    $505,000 Sold Sep 26, 2025

    02 John Hoft Rd Unit 2, Tisbury, MA 02568

    • Land
    • 1.3 Acres
    • $388,462 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 120 Days On Market

    Last Listing Agent Tony Tobia Tobia Real Estate, LTD

    02 John Hoft Rd Unit 2, Tisbury, MA 02568
    • /19

      Est $1,303,129 Not Listed For Sale

      46 Windsor Dr, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,520 Sq Ft
      • Built 1987
      46 Windsor Dr, Edgartown, MA 02539

      Last Sold Summary

      • 9% Above List Price
      • $786/SF
      • 22 Days On Market

      Last Sold Price $1,195,000

      Last Listing Agent Francine Agnoli The Agency Martha's Vineyard

  • /19

    $10,500,000

    • 5 Beds
    • 2.5 Baths
    • 2,794 Sq Ft

    33 Goethals Way, Vineyard Haven, MA 02568

    A rare opportunity -- a Vineyard harbor front property with a Victorian gambrel cottage restored to its original grandeur of a century ago, an expansive front yard, 180 degree commanding views of the active harbor, private sandy beach, and unmatched serenity. You have the opportunity to own one of the finest estates gracing the Vineyard Haven harbor front -- so admired by all visitors to the

    Buder Team Sandpiper Realty, Inc.

    33 Goethals Way, Vineyard Haven, MA 02568
  • /35

    $22,000 total monthly price

    • 4 Beds
    • 2 Baths
    • 2,290 Sq Ft
    • House for Rent

    36 Henry Hough Lane Ch206, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four

    Karen Overtoom Karen M. Overtoom R.E.

    36 Henry Hough Lane Ch206, Chilmark, MA 02535
  • /38

    $1,500,000 Sold Jan 23, 2026

    128 W Spring St, Vineyard Haven, MA 02568

    • 5 Beds
    • 3.5 Baths
    • 2,436 Sq Ft
    • Built 2013

    Last Sold Summary

    • 14% Below List Price
    • $616/SF
    • 145 Days On Market

    Current Estimated Value $1,220,868

    Last Listing Agent David Dickinson Compass

    128 W Spring St, Vineyard Haven, MA 02568
    • /22

      Est $4,388,798 Not Listed For Sale

      1 Skippers View Ln, Aquinnah, MA 02535

      • 4 Beds
      • 3 Baths
      • 2,905 Sq Ft
      • Built 2001
      1 Skippers View Ln, Aquinnah, MA 02535

      Last Sold Summary

      • 4% Below List Price
      • $1,575/SF
      • 0 Days On Market

      Last Sold Price $4,575,000

      Last Listing Agent Rebecca V Conroy Conroy & Company R.E., Inc.

  • /7

    $795,000 Pending

    • Land
    • 2.52 Acres
    • $315,476 per Acre

    0 W End Rd, Gosnold, MA 02713

    Vacant, buildable, water-view lot comprised of 2.52 ± wooded acres with subdivision potential and views of Martha’s Vineyard and Vineyard Sound. Buyer should do their own due-diligence on subdivision. Located on Cuttyhunk Island, part of the Elizabeth Islands off the southern coast of Massachusetts is located between Buzzards Bay and Vineyard Sound. At just 550± acres Cuttyhunk Island offers a

    Slater Anderson LandVest, Inc.

    0 W End Rd, Gosnold, MA 02713
  • /39

    $110,000 total monthly price

    • 5 Beds
    • 5 Baths
    • 4,000 Sq Ft
    • House for Rent

    17 Round Pond Rd Ch240, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. See web site for pricing!! Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches and high speed internet wifi.

    Karen Overtoom Karen M. Overtoom R.E.

    17 Round Pond Rd Ch240, Chilmark, MA 02535
  • /42

    $1,700,000 Sold Nov 03, 2025

    35 Tower Ridge Rd, Oak Bluffs, MA 02557

    • 3 Beds
    • 4 Baths
    • 2,558 Sq Ft
    • Built 1986

    Last Sold Summary

    • 20% Below List Price
    • $665/SF
    • 118 Days On Market

    Current Estimated Value $1,733,257

    Last Listing Agent Katherine Donahue Sandpiper Realty Inc

    35 Tower Ridge Rd, Oak Bluffs, MA 02557
    • /2

      Est $1,786,989 Not Listed For Sale

      11 Deacon Vincent Way, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,250 Sq Ft
      • Built 1986
      11 Deacon Vincent Way, Edgartown, MA 02539

      Last Sold Summary

      • 7% Above List Price
      • $1,340/SF
      • 34 Days On Market

      Last Sold Price $1,675,000

      Last Listing Agent Courtney Marek Sandpiper Realty Inc

  • /30

    $1,595,000

    • 5 Beds
    • 3 Baths
    • 1,810 Sq Ft

    22 Old Lighthouse Rd, Vineyard Haven, MA 02568

    Located in a quiet enclave off Main Street, Vineyard Haven and just a half-mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels featuring hardwood floors, a cozy fireplace, and a seamless layout, the home is ideal for entertaining. The design is casual but practical,

    Jessie Holtham Wallace & Co. Sotheby's International Realty

    22 Old Lighthouse Rd, Vineyard Haven, MA 02568
  • /19

    $24,000 total monthly price

    • 4 Beds
    • 4 Baths
    • 2,000 Sq Ft
    • House for Rent

    44 Flanders Ln, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

    Karen Overtoom Karen M. Overtoom R.E.

    44 Flanders Ln, Chilmark, MA 02535
  • /30

    $1,995,000 Sold Aug 29, 2025

    26 Box Turtle Ln, Oak Bluffs, MA 02557

    • 4 Beds
    • 3.5 Baths
    • 2,891 Sq Ft
    • Built 1980

    Last Sold Summary

    • $690/SF
    • 5 Days On Market

    Current Estimated Value $2,037,182

    Last Listing Agent Jayne Isford Ocean Park Realty Inc

    26 Box Turtle Ln, Oak Bluffs, MA 02557
    • /39

      Est $6,131,941 Not Listed For Sale

      103 Main St, Vineyard Haven, MA 02568

      • 5 Beds
      • 6 Baths
      • 6,546 Sq Ft
      • Built 2008
      103 Main St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 49% Below List Price
      • $1,833/SF
      • 202 Days On Market

      Last Sold Price $12,000,000

      Last Listing Agent Tom Wallace Wallace & Co. Sotheby's International Realty

  • /7

    $1,575,000

    • 2 Beds
    • 1 Bath
    • 924 Sq Ft

    47 Quenames Rd, Chilmark, MA 02535

    On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural

    Dawn Bellante Sandpiper Realty, Inc.

    47 Quenames Rd, Chilmark, MA 02535
  • /32

    $36,000 total monthly price

    • 3 Beds
    • 3.5 Baths
    • 2,600 Sq Ft
    • House for Rent

    29 Cemetery Rd Ch216, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half

    Karen Overtoom Karen M. Overtoom R.E.

    29 Cemetery Rd Ch216, Chilmark, MA 02535
  • /18

    $995,000 Sold Nov 06, 2025

    2 Flamingo Dr, Edgartown, MA 02539

    • 3 Beds
    • 1 Bath
    • 990 Sq Ft
    • Built 1983

    Last Sold Summary

    • 5% Below List Price
    • $1,005/SF
    • 5 Days On Market

    Current Estimated Value $1,071,987

    Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate

    2 Flamingo Dr, Edgartown, MA 02539
    • /34

      Est $1,565,448 Not Listed For Sale

      84 Christiantown Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,452 Sq Ft
      • Built 2018
      84 Christiantown Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 12% Above List Price
      • $964/SF
      • 59 Days On Market

      Last Sold Price $1,400,000

      Last Listing Agent Candy DaRosa Feiner Real Estate

  • /42

    $9,499,000

    • 4 Beds
    • 7 Baths
    • 5,902 Sq Ft

    43 Peases Point Way S, Edgartown, MA 02539

    Refined, timeless, and unparalleled, 43 Peases Point Way South effortlessly blends warmth, elegance, and sophistication to create a truly distinctive living experience in one of Edgartown's most coveted locations. Designed by celebrated architect Patrick Ahearn, this exceptional residence is just a short stroll from historic Main Street. From the gated arbor entry and tranquil courtyard to the

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    43 Peases Point Way S, Edgartown, MA 02539
  • /29

    $64,000 total monthly price

    • 4 Beds
    • 7 Baths
    • 3,600 Sq Ft
    • House for Rent

    385 Barnes Rd Ob534, Oak Bluffs, MA 02557

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in

    Karen Overtoom Karen M. Overtoom R.E.

    385 Barnes Rd Ob534, Oak Bluffs, MA 02557
  • /44

    $1,890,000 Sold Aug 29, 2025

    1 Thames Ct, Edgartown, MA 02539

    • 4 Beds
    • 3 Baths
    • 3,270 Sq Ft
    • Built 1981

    Last Sold Summary

    • $578/SF
    • 38 Days On Market

    Current Estimated Value $2,091,469

    Last Listing Agent Jon Hartzband Martha's Vineyard Island-Wide Realty

    1 Thames Ct, Edgartown, MA 02539
    • /30

      Est $1,794,619 Not Listed For Sale

      8 Harpoon Hollow, Aquinnah, MA 02535

      • 3 Beds
      • 3 Baths
      • 2,046 Sq Ft
      • Built 1940
      8 Harpoon Hollow, Aquinnah, MA 02535

      Last Sold Summary

      • 12% Above List Price
      • $782/SF
      • 179 Days On Market

      Last Sold Price $1,600,000

      Last Listing Agent Brenda Galligan Karen M. Overtoom R E

Showing Results 161 - 200, Page 5 of 18

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